


Isn't it Messed Up, How I'm Just Dying to Be Him?

by JustAWinchesterGirl



Category: Supernatural
Genre: All smut, Dom!Cas, Dom!Sam, Incest, M/M, Sub!Dean, Voyeur!Sam - Freeform, Wincest - Freeform, it's not really Destiel and it's not wincestiel but there are hints of that happening as well, its Wincest, just lots of sex, literally completely PWP, mentions of underage but no actual underage happened, there's so much in this idk what to tag, this is a Wincest fic but there is some Cas at the beginning
Language: English
Status: Completed
Published: 2016-05-28
Updated: 2016-05-28
Packaged: 2018-07-10 16:25:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,420
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6995062
Author URL: https://archiveofourown.org/users/JustAWinchesterGirl/pseuds/JustAWinchesterGirl
Summary: <blockquote class="userstuff">
              <p>Sam can’t see Dean’s cock or what Cas is doing to it from where he’s watching, but he doesn’t have to- he’s watched them enough to know what it looks like when the tip of the angel’s pink tongue trails along his older brother’s dick, when his lips wrap around the tip and he sucks, when Dean fucks his mouth so that he’s breathing hard through his nose and there’s saliva dribbling down his chin, when Dean comes in his mouth and on his face and then Cas makes him lick it up. He knows what it looks like. He’s been watching for a long time.</p>
<p>Wincest. PWP. Inspired by "Sugar, We're Going Down" by Fall Out Boy.</p>
            </blockquote>





	Isn't it Messed Up, How I'm Just Dying to Be Him?

“Fuck! Cas! God, Cas! Yes!”

Sam’s fighting to control his breathing as he peeks through the crack in the door into Dean’s bedroom. Dean’s sitting on the end of the bed, naked, legs spread wide with Castiel on his knees between them. Sam can’t see Dean’s cock or what Cas is doing to it from where he’s watching, but he doesn’t have to- he’s watched them enough to know what it looks like when the tip of the angel’s pink tongue trails along his older brother’s dick, when his lips wrap around the tip and he sucks, when Dean fucks his mouth so that he’s breathing hard through his nose and there’s saliva dribbling down his chin, when Dean comes in his mouth and on his face and then Cas makes him lick it up. He knows what it looks like. He’s been watching for a long time.

So even though he can only hear the sounds, and can only see Dean’s face and the back of Castiel’s head- he’s rock hard under his jeans and trying desperately not to palm himself through the course fabric, because if he does he’ll almost certainly make noise and he doesn’t want to get caught.

He doesn’t want Dean to know how sick he is- watching his brother have sex with an angel. Because as beautiful as Castiel is, Sam is most definitely not here for him. He’s not here to admire Cas’ body, or the way he looks when he comes undone. No. He’s here to watch his beautiful brother get wrecked by Heaven’s fallen.

He hears the sound of Cas pulling wetly off of Dean’s dick, and Dean’s responding irritated groan, and sneaks another peek through the crack in the door.

Cas is standing now, absurdly clothed in comparison to Dean, but Sam can’t spare a second thought for that now- not while Dean is all spread out and on display, face wrecked, chest heaving, and cock red and wet and hard.

Sam’s mouth is dry and his cock is beginning to hurt straining against his pants, and he lets himself pop the button on his jeans open.

“Cas, please,” Dean begs, voice wrecked and gravelly and Sam thinks he might come just listening to it.

“Dean,” Cas says, too calmly for what he’s being allowed to do, “You know the rules.”

“Fuck,” Dean groans, but he gets off the bed and onto his knees on the floor in front of the angel to await his next orders, and fuck how sick is it that Sam wants nothing more than to be where Cas is? To have full control of his brother’s body, just for one day even, just to see what he could do to him, to see if he could make him look that wrecked.

Sam watches the angel shed his coat, open up his jeans, and pull his cock out, and Dean doesn’t even get a second to take it all in before Cas’ hand is tugging roughly at his hair and he’s fucking his mouth.

The angle is much better now and Sam says a silent _thank god_ because Dean is never more beautiful than when his full pink lips are wrapped around a cock.

His face is red, and his eyes are watering, and his throat muscles contract as he chokes on Cas’ dick and struggles to keep up with the angel’s brutal pace, but he’s moaning loudly and with utter abandon around Castiel’s cock and his fingers twitch where he’s keeping his hands behind his back as he tries not to touch himself.

Then, all at once, it stops and Sam watches as Dean tries to inch his way back toward Castiel’s cock but is pulled roughly back by his short hair and he cries out in pain and pleasure, and Sam _has_ to touch himself through his boxers just a little.

“Cas,” Dean croaks, throat raw and fucked dry.

“Do you want me to come in your mouth, Dean?” the angel asks, still too calm and eloquent for how painfully hard he looks.

“Yes! Yes, please, Cas!” Dean moans and Sam’s dick twitches at the thought of his brother begging **him** like that.

“Are you sure?” he asks, “I can come in your mouth, Dean, or I can fuck you. This time you can choose.”

Dean moans loud and low, and his head rolls back into the grip the angel still has on his hair, “Fuck, Cas! Fuck me, please!”

Cas gives him a small smile and releases him, beginning to strip off the rest of his clothes, but still Dean doesn’t move until Cas says, “On all fours on the bed, Dean.”

Dean crawls onto the bed, facing him and Sam goes back behind the wall for fear of being seen.

He can hear the bed shift as Cas kneels behind him, and the pop of a bottle cap as he opens the lube. Sam closes his eyes and imagines it’s him behind his brother instead, working him open on his fingers, his tongue, getting him ready to fuck. He imagines those moans, and whimpers, and breathy pleas for more are for him, for the way he touches and kisses and takes care of Dean.

Sam’s not one to tell an angel what he can and can’t do, but Cas doesn’t deserve Dean like this in Sam’s opinion. He doesn’t appreciate it enough, not like Sam would. Cas doesn’t even moan, doesn’t make a noise, doesn’t kiss Dean’s lips the way he deserves, doesn’t hold him afterward.

Though, Dean never seemed to mind. Dean would always come undone under Cas with reckless abandon, Castiel’s name on his lips like a prayer, then the angel would disappear and the next day Dean would pretend nothing had ever happened.

Sam had been witness to many of Dean’s sexual exploits growing up. He’d seen him drunkenly stumble in and out of motel rooms with hot blonde after hot blonde in both the man and woman variety, and he had never looked the least bit ashamed or like he had anything to hide.

Was he worried Sam would judge him because Cas was an angel?

He sneaks another peek when he hears Dean moan and the sounds of skin slapping against skin that tell him Cas has started to fuck him. It’s dangerous to look now because they’re both facing him, but Sam can’t help himself.

He can’t see much of Cas behind Dean, but he doesn’t care about that. What he can see is everything he’d come here to see in the first place. Dean, rocking quickly on his hands and knees as Cas fucks him roughly, cock slapping against his belly as they move, his face screwed up in pleasure, eyes closed and mouth open, moaning incoherently and begging the angel for more.

Sam wishes more than anything that it was him. And how fucked up is that? How fucked up is it that no one else could make Sam this hard? No one else could make him ache for it this much. Ever since he was fourteen and started getting turned on by things, he was never more turned on than when he was watching his brother. God, Dean had never even touched him, and already he was wrecked for anyone else. Sam only had one desire and that was Dean. How he longed to be in Castiel’s place. How he wished it were his name falling from his brother’s lips like that.

His hand works slowly over his cock and he tries to keep himself quiet as he works himself closer to the edge to the sounds of his brother’s moans, every so often sneaking a peek when he thinks it’s safe to do so.

When Cas comes, he finally makes a noise. A strangled sort of moan that he always looks surprised at. Dean comes with a moan of Cas’ name wrenching itself from his lungs to fill the air around them and Sam’s too far gone to stop now so he allows himself to come quietly in his shorts while Dean’s moans are stifling his sounds.

But when he comes down he hears Dean say, “Sam?” in a timid, ruined voice and hears Cas get off the bed to walk toward the door and maybe he’d moaned Dean’s name just a little too loudly when he came.

“Sam,” Cas says seriously, pushing the door open to reveal him to Dean, standing there with his jeans pushed partway down his thighs, his hand still wrapped around his softening cock through his boxers, come cooling on his stomach and in his shorts.

“I didn’t- This isn’t- I-,” Sam tries, but he can’t get the words out. What even are the words? What could he possibly say in this situation?

“Sam,” Dean says again, crawling off the bed, but making no move to cover himself, “What- what the hell, dude?”

“I- I don’t-,” he starts, but Dean cuts him off, chuckling.

“You _still_ like to spy on me? I thought you stopped doing that when you were like seventeen.”

Sam’s eyes widen in terror, “What?”

Dean smirks, “You think I didn’t know?”

“You never said anything,” Sam mumbles.

“You were a kid, Sam,” Dean says, “You were loud. And serious jailbait, too.”

Sam’s eyes snap up to meet Dean’s and his big brother is smiling at him much too smugly for what Sam had just witnessed.

“Why didn’t you ever tell me? If you knew that I… that I…”

“Wanted to fuck your brother?” he laughs, “You went away to school Sam. You got over me. Or, I thought you did. Thought you’d realized how absolutely _fucked_ that is. Turns out I was wrong.”

“It is fucked. I’m fucked,” Sam mumbles.

“ _We’re_ fucked,” Dean corrects, grabbing Sam by the collar and pulling him down into a rough, bruising kiss.

Dean kisses all the questions and worry right out of Sam’s mouth. Tongue licking past his lips and over his teeth, curling against him and delving into the corners of his mouth. Sam can taste Cas on Dean’s tongue and he sucks on it, wanting to get every bit of the angel out of Dean’s mouth and replace it. When Dean pulls away, he tugs on Sam’s lip between his teeth before smiling at him and raising an eyebrow in question at his brother.

“What about Cas?” Sam asks reluctantly, finally looking at the angel, who doesn’t look angry, or embarrassed, or uncomfortable at all.

“What about him?” Dean asks.

“Would you like me to stay?” Cas asks, looking slightly confused, “I was under the impression you were only here for Dean.”

“I- No. I am. I just- you two aren’t… together, or anything?” This is okay with you?” Sam asks awkwardly.

Dean chuckles, “No, man. We ain’t a couple. This is it.”

Sam’s cheeks burn red and he can feel himself start to grow hard again at his vivid memories of what “it” is.

“Yes, well. I suppose I better leave,” Cas says, and Sam wonders how he can sound so innocent after the way he’d just been filthily ordering around Dean and using him like a sex doll.

Cas disappears and Sam is forced to look at Dean again, who is still very naked, smirking at him, and surprisingly growing hard again.

“So?” Dean says quietly, eyes glinting in mischief as he takes a step toward Sam, “You like to watch, little brother?”

Dean’s close to him now, chest almost pressing against his, and he reaches up and grabs Sam’s jaw, turning his head to make him look at him, tongue running over those perfectly pink lips.

“Yes,” Sam breathes.

“How long you been watching Cas fuck me, huh? DO you like watching your big brother get fucked on angel cock?” he doesn’t even look embarrassed. He doesn’t look anything but turned on.

Sam shakes his head as much as he can in Dean’s grip, “I like to pretend it’s me.”

Dean groans, “Always? Even when you were little? It was always me getting fucked?”

“No,” Sam admits, “sometimes I… I finger myself and pretend it’s you.” Dean moans in response, and Sam feels like a teenager again, hot and embarrassed at admitting these things out loud, “But god, Dean, if I knew back then you were this much of a fucking sub…” he says, swallowing his fear and trying to match his brother’s bravado, “You have no idea how much I wanna fuck you.”

“Fuck, Sammy,” Dean breathes, “If Cas hadn’t just fucking spent me, I’d be twice as hard by now.” His eyes dart down Sam’s body, “But despite having just come in your pants like a fucking teenager, you don’t seem to be having the same problem.”

Dean sinks to his knees in front of him before he can even fathom what’s happening and wraps his lips around Sam’s cock the minute he gets it out.

Sam moans loudly and rakes his fingers through his brother’s hair as his skilled tongue runs over his cock.

“Fuck, Dean!” he gasps.

And if Sam thought Dean looked best with a cock in his mouth, then when it was _Sam’s_ cock he was downright gorgeous.

Sam was bigger than Cas in every sense of the word, and Dean’s lips were stretched wide around the end of his dick, his tongue teasing the head and underside to make up for the fact that he was not going to be able to take him all in. Sam’s actually surprised when he feel himself hit the back of Dean’s throat, and Dean moans around him like it’s the best feeling in the world, like his throat hadn’t just been fucked raw by the angel that had him before Sam.

He’d love nothing more than to fuck Dean’s mouth, to watch his big brother swallow his cock again and again and moan for him the way he was now, but his cock was still sensitive from his first orgasm and he didn’t want to come down his brother’s throat this time. So he grabs Dean by the hair and pulls his dick out of his mouth, smiling at the little noises Dean makes in protest.

“ _Sammy_ ,” Dean whines, looking up at him through those goddamn long lashes, green eyes watering, pink lips plump and wet with spit. He looks like a goddamn porn star and Sam can hardly believe he’s not dreaming.

“No,” Sam says sternly, grip still on his brother’s hair, surprising even himself a little, “If you want to taste my come so badly you can lick it off my stomach.”

Dean’s eyes light up in excitement when Sam takes control, naturally falling into a position to obey despite the fact that this is _Sam_ and he wants to put up a bit of a power struggle.

“Good,” Sam chuckles, “It’s not just Cas you listen to.”

Dean smirks, “Oh fuck, Sammy, I wanna slam you against the fucking wall and show you a new meaning to the words ‘sibling rivalry’, but I’m too excited to see what you’ve been planning for all these years.”

Sam laughs, “Oh, we’ll get to all of that one day. For now, I’m thinking you deserve a little payback.”

Dean raises an eyebrow at him, keeping his bravado, but he looks a little worried, “Payback?”

“Yes, Dean, payback,” Sam answers, a little more confidently, circling his brother and trailing his fingertips lightly over the skin of his shoulders as he speaks, “for all of the times you let your poor little brother take care of himself quietly in a closet or a motel bathroom when you knew all he wanted was for you to touch him. For every time you thought about me- because it’s clear now that you have- and did _nothing_.For every drunk girl or ‘experimenting’ football jock you made me watch you have sex with while we were growing up, when you knew I was more than willing to warm your bed if only you had _asked_.”

Dean shudders in response, biting back a moan at Sam’s words, and not daring to speak or move until he is told.

“I practically worshipped you growing up, Dean,” Sam continues, “I wanted to be just like you, but you knew that. You knew how much I loved you. But did you know how much I wanted you to fuck me? Before I even really knew what sex was I was touching myself to the thought of you on me, Dean.”

“ _Fuuuuck_ , Sammy!” Dean groans, forgetting himself, “This is torture.”

“This is just the beginning,” Sam smirks, “I told you, I’m getting payback. I’m just gonna make you watch. I’m gonna get myself off moaning your name and you’ll just have to kneel there and watch me.”

Dean groans again, tipping his head back, “Sam!” he protests, “After waiting so long for me? You could just jerk yourself off again? When I’m _right here_ to take your cock any way you want me to?” He smirks and bites his lip.

“Do not think you can get out of this that easily,” Sam says, starting to shed his clothing as he walks toward the bed and Dean turns, still on his knees, to face him. Sam fully intends for _one of them_ to get fucked tonight, but first thing is first.

“Did you ever think about this, Dean?” Sam asks as me reclines on the bed, propping himself up on one elbow, spreading his bent knees and slowly beginning to jerk his cock while he watches his brother’s face, “Did you ever get off to the thought? You already know I did.”

Dean only moans.

“I asked you a question, Dean.”

“Fuck! Fuck, **yes** , Sammy,” Dean groans.

“Tell me what you thought about,” Sam demands, still slowly jerking himself off, eyes locked with Dean’s lust blown ones.

“Fuck,” Dean breathes again, struggling not to touch himself and trying to keep his eyes on Sam’s instead of his cock, “Fuck, I- you were sixteen when I caught you the first time, and I… you were so small back then, Sam, so innocent… but the way you moaned my name while you were fisting your cock. You were downright x-rated, little brother. Kept wondering how my name would sound coming out of your mouth if you were choking it out around my cock.”

Sam moans and his eyes break contact with his brother’s as his head falls back, “God, I wanted to, Dean,” he huffs.

“Imagined what pretty sounds you’d make if I bent you over and fucked you into the table,” Dean goes on, enjoying the effect he’s having on his brother. He wasn’t entirely sure who was in control here now, but he stayed in his submissive position and didn’t touch himself until Sam said. “Then after Stanford, you were suddenly so much bigger than me. You hit a huge fucking growth spurt, I guess, and filled right out. Fuck, Sam, do you even know how hot you look? Wanted to ride your dick in the cramped backseat of my car since the moment I picked you up.”

“Then… why- why didn’t you?” Sam pants.

“ _Brothers_ , Sam. We’re brothers,” Dean chuckles.

“So?” Sam asks, eyes back on Dean’s as he eases up on his dick, sitting up slightly more to face Dean better. His fingers slip down from his cock to circle at his entrance and Dean’s mouth goes dry.

“Gonna fuck yourself on your fingers for me, little brother?” Dean manages to get out and maybe even still sound like he isn’t ruined inside.

Sam moans and bites his lip, “Maybe. If you know where Cas put that lube.”

“Fuck. It’s under the pillow,” Dean says. His knees are beginning to ache and he wants to get up and fuck his little brother into the mattress, but Cas has trained him to be a _Good Boy_ , and fuck if that’s gonna stop now. He’s always learned that discomfort like this gets you the ultimate reward later and fuck if his mouth doesn’t just water at the thought of what that reward might be with Sam.

When Sam slicks his fingers and slips one knuckle deep inside himself, Dean’s not sure if he moans or if Sam does. He wants to touch himself. He wants to touch Sam. He wants to put his mouth on him, _anywhere_ on him.

“Sam, man, please,” he begs, watching Sam’s cheeks turn a pretty shade of red as he basks in the pleasure he’s giving himself.

“ _Dean_ ,” Sam moans, fucking himself on his finger and quickly slipping a second in alongside it, “Come here.”

“Fuck, finally,” Dean sighs, practically bounding off of his knees and onto the bed in front of his brother.

Sam reaches out with his free hand and takes Dean’s, guiding him toward the head of the bed. “Sit,” Sam orders, gesturing at the pillows. Dean settles back against them, eyes never leaving his brother as he eagerly awaits his next move.

Sam pulls his fingers from himself and crawls over his brother, straddling his lap and wrapping his hands around his neck to pull him up for a heated kiss. Dean licks at his brother’s lips eagerly, sighing into Sam’s mouth when he nips Dean’s bottom lip hard enough to bruise and forces his tongue inside his mouth. His hands are tangled in that long brown hair that he has always wanted to pull ever since Sam had it long enough for a ponytail. He wonders how it would look wrapped around his fist while Sam chokes on his dick.

He begins to wonder how it’s even possible for that thought to make him harder at this point, when Sam grinds down against him and all thoughts cease to exist. He moans, loud and wanton into his brother’s mouth and Sam chuckles, but it’s breathless and needy and Dean can tell his little brother is just as far gone as he is.

“Sammy,” he whines, desperate for something, anything else.

“What- what do you want, Dean?” he asks in a shaky voice.

“Wanna… wanna be inside you, baby brother,” Dean gasps as Sam takes his cock in one big hand and starts to stroke him slowly, “Want… want you to- _fuck, Sam_ \- want you to ride my cock. Want you to take whatever you need, Sammy. Use me. _I’m yours_.”

“ **Fuck!** ” Sam practically growls, and lowers himself onto his brother’s cock slowly.

Dean’s struggling like hell not to blow his load just from this, digging his fingers into his brother’s bony hips and trying not to thrust himself deeper into his tight heat.

When Sam’s sunk all the way down onto Dean’s cock, he stills, eyes closed, and takes a deep breath through his nose. He’d always imagined what it would be like to bend Dean over, face in the pillow, and fuck him hard and fast the way that Cas did. But having Dean fill him up- there to fuck himself on and use for his pleasure- that was even better. Because this was something Castiel never did. This was all for him.

Slowly, he lifts himself almost all the way off his brother, enjoying the way it feels to have Dean’s cock moving inside of him, and drops himself back down.

Dean hisses and his head falls back against the wall, his eyes falling shut and Sam does it again, starting a slow but steady pace.

“God, Dean,” he moans quietly, hands squeezing at his brother’s shoulders where they’re resting for leverage, “Fuck this feels good.”

Dean whimpers in response, eyes squeezed shut tight as he tries desperately not to just grab his brother’s hips and slam into him.

Sam leans forward and captures Dean’s lips with his, kissing him fiercely. They kiss until their lips are chapped and swollen and their lungs burn, and Sam’s riding Dean’s dick faster, slamming himself down desperately as his lips work against his brother’s.

“Fuck, Sam,” Dean gasps against his brother’s lips, “Can’t- gonna come inside you, baby brother.”

“Fuck, Dean, please,” Sam groans, leaning slightly forward and grinding on his brother’s cock, “Wanna feel you.”

Dean reaches between them and wraps his hand around Sam’s cock and starts to jerk him, matching the pace Sam is riding him at. Dean looks up at his brother’s face and is met with those big dark eyes staring back at him, heavy with lust and gazing at him through thick lashes, his face pink and his breath coming in heavy pants.

“Dean,” he breathes, and he sounds so wrecked and so desperate Dean just can’t hold on any longer, he throws his head back and moans his brother’s name and comes hard while Sam rides him.

Sam doesn’t stop, he’s gripping Dean’s shoulders and clawing at his back and riding him even harder. There’s come leaking down over his balls and down his thighs, and Dean whines, becoming soft and oversensitive inside his brother. This is his second orgasm tonight and Sam’s riding his softening cock with everything he’s got.

He won’t complain though. He’s a good boy, and he’s Sam’s to use.

Sam replaces Dean’s hand around his cock with his own, fisting himself as he rides his brother with reckless abandon, chasing his second orgasm as well. His other hand grips Dean’s jaw tightly and yanks his head up to look him in the eyes.

“Do you like this, Dean?” Sam huffs, “Do you like knowing it’s your little brother you’re fucking? That it’s your little brother you just shot your load inside?”

“Sammy-”

“Do you?”

“ **Yes** ,” Dean moans, and Sam smirks, tongue darting out to moisten parted pink lips and suddenly he tips his head back and _moans_ , coming in spurts between them, soaking his hand and both of their bellies. Sam slumps against his brother’s chest, squishing the rapidly cooling come between them, panting into his neck.

“You’re mine, big brother,” Sam puffs against his skin, “No one else’s.”

Dean nods weakly, “Yours,” he agrees.

“Not even Cas,” Sam goes on.

“Okay,” Dean gasps as Sam finally slides off him.

“Really?” Sam asks, turning to look at him seriously.

“Of course, Sammy,” Dean says, nonchalantly, “I meant it. I’m yours, little brother.”

Sam’s grin splits his face and Dean’s breath catches in his throat.

“Dean…” Sam breathes.

“Don’t. Don’t go and make it sappy, Sam,” Dean says, but he’s grinning.

Sam laughs, “Okay. And hey, Dean?”

“Yeah?”

“I could maybe share you sometimes… I still like to watch.”


End file.
